


Dear Dean Winchester

by httpsashtrid



Category: Supernatural
Genre: Dean Sings, Gen, High School, Musicals, Weechesters, dear evan hansen - Freeform
Language: English
Status: In-Progress
Published: 2017-06-20
Updated: 2017-06-20
Packaged: 2018-11-16 09:18:44
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,899
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11250165
Author URL: https://archiveofourown.org/users/httpsashtrid/pseuds/httpsashtrid
Summary: The principal of yet another nameless high school forced Dean to take drama class to learn teamwork or some crap. He didn't care.One day Dean is cast as Evan Hansen, the lead of the school musical.





	1. Chapter 1

God it was so stupid how he got here. Lights shining in his face. People staring up at him from a few feet below him in little seats while he stood on the stage, reciting lines.

 

Let's back up a bit.

 

**TWO WEEKS BEFORE**

 

"You kids didn't know this, but I've been keeping an especially close eye on some of you. Watching your mannerisms. How you act around your friends. In other classes. Things like that," the drama teacher said. She was a gorgeous young woman, probably fresh out of college.

 

"Um, scary," one of Dean's friends, Matt, said. The class laughed. Dean swat at Matt, grinning.

 

"Take what you can get, Matty, because she's the only girl who's ever gonna bat you an eye," Dean joked. The class laughed louder. Matt punched him in his shoulder.

 

"That may be true, but the only reason girls look at you is because you look like a Disney princess, with your long eyelashes and blond hair," he shot back. Despite the fact that Matt was joking, insecurity stabbed at Dean. He hated that he looked so girly. He hid this, of course, and no one was any the wiser. Expect Miss Marie Ray.

 

She saw the insecure and needy boy beneath this facade that Dean Winchester put up. He saw the flash of hurt that went through Dean's eyes. That degree in psychology wasn't for just nothing. She's been thinking about having Dean cast as Evan Hansen since the day he walked into her class two months ago, his hands shoved in his pockets and examining the class with watchful eyes.

 

"Alright, alright. That's enough. Getting back to the topic at hand, North Oaks High School is proudly presenting Dear Evan Hansen, an original musical written by yours truly," Ray said, smiling. Most of the class smiled and cheered. The people who complained were Dean, Matt, Brian, and Casey.

 

"Aw, what the hell?"

 

"I'm SO not doing that!"

 

"Singing is for chicks!"

 

"Jesus Christ, what have I gotten myself into?"

 

"Well maybe if you four didn't keep getting in trouble, you wouldn't have been forced into this class. Perhaps now you'll think before you start fights in the locker room," Ray raised an eyebrow.

 

"Some asshole was messing with my little brother. I wasn't gonna stand for that. If anyone should be in trouble, it should be me because I beat the hell out of that guy for calling my baby brother a fag," Dean shot out.

 

"Is that so? Then you wouldn't complain about staying after school and helping find props from the closet, would you?" Ray answered. Dean's eyes widened.

 

"But I have to get Sammy from school after I get out of here. He's gonna think I forgot about him or something, and, man, he's gonna freak out for a week," Dean protested.

 

"Alright. I'll make it simple for you. Go get your brother and take him home, then come back. By 4:30. If not, you'll be expelled. He's going to think a lot less of you if he finds out his big brother got expelled because you didn't go to a detention that you highly earned," Ray said. The bell rang, and the students got up. "Bye class! See you after school, Dean!"

 

"Son of a bitch," Dean muttered.

 

________________________________

 

"Dean!" 12 year old Sammy yelled and ran into his arms. Dean grunted when Sam's weight slammed onto his chest.

 

"Hey Sammy," Dean hugged him back. "How was school?"

 

"We learned about Hamilton, De!" Sam said.

 

"Oh yeah? What did he do?" Dean questioned, smiling at Sam's enthusiasm.

 

"He wrote, like, EVERYTHING. All the time. He never stopped!" Sam exclaimed.

 

"That's awesome, kiddo," Dean said. He grabbed Sam's hand and walked to the public bus stop with him. "Um.. Sammy?"

 

"Yeah?" Sam asked slowly.

 

"I... Forget it. You're just gonna come with me. I don't trust leaving you at the motel by yourself for two hours," Dean shook his head.

 

Sam sighed. "What did you do, Dean?"

 

"Got detention. Its okay though. I'm just helping the theater teacher with some play that we're doing."

 

"We? You're in it, Dean?" Sam sounded shocked.

 

"What? Ew. No," Dean said quickly. "I'm just going to help her."

 

"Right," Sam said.

 

_________________________________

 

"Miss Ray! I'm here!" Dean called when he walked into the auditorium.

 

"I'm back here, Dean!" Ray called from back stage.

 

"Come on, Sammy," Dean guided him to where Miss Ray was. When he found her, she was buried deep into a closet of costumes from years before.

 

"Nice to see you, Dean. This must be the famous Sammy," Ray said, smiling.

 

"It's Sam," Sam said, blushing.

 

"Yeah. I couldn't leave him at home like that by himself. He could burn the house down, and I'd be none the wiser," Dean said. "Hope you don't mind I brought him."

 

"No its fine. May I ask where your parents are?" Ray asked.

 

"Mom died when we were kids, and Dad is off on business," Dean answered. Ray could see the pain hidden in Dean's eyes.

 

"Oh, I'm sorry," Miss Ray said. Dean just nodded. "Well here's what I need you to do. I need you to find a desk back there first. Then as many normal guy looking clothes as possible. Things that you'd wear."

 

"Dean only wears faded band shirts, plaid, and his leather jackets," Sam said.

 

"And where's the problem in that?" Dean looked at him with a raised eyebrow.

 

"You don't know how to dress, Dean, that's all I'm saying."

 

"Suddenly you're the fashionista? It makes sense because you spend 4 hours fixing your hair, Samantha," Dean teased. Sam rolled his eyes.

 

"Shut up, jerk."

 

"Bitch."

 

"Alright you two," Ray said. "Sam, would you like to come with me and help make some of the backgrounds?"

 

"Sure," Sam smiled.

 

"Is that okay, Dean?" Ray asked. Dean hesitated at first.

 

"Yeah, sure. Whatever he wants to do," he said.

 

"Thanks, De!"

 

"Go paint, weirdo," Dean smiled despite himself. Sam laughed and walked off with his teacher.

 

Dean stretched and sighed. He looked around and saw a radio sitting where Ray was sitting. He grinned and played with the knob before he found a classic rock station. Before going to the back, he turned it up.

 

"Bad Reputation" by Joan Jett and the Blackhearts came on. What started as humming became singing under his breath as he imagined himself in front of a huge crowd screaming his name. It brought a wide smile to his face as he spun around, grabbing a box of clothing he found. In the back of a stack of other boxes, he found the desk Miss Ray wad talking about. Thankfully, it had wheels on it. He placed the box of clothing on top of it and wheeled it out, still singing.

 

The song ended, and he laughed a little. He turned around and jumped whenever he saw Ray behind him, his hunter mode flicked on. His fists came up immediately.

 

"Jesus Christ, lady! Don't sneak up on a guy like that!" Dean gasped, relaxing once he realized who it was.

 

"Sorry. I heard you singing, and I just wanted to say that you have a beautiful voice," Ray said. Dean blushed.

 

"Nah. I can't sing at all. I was just humming," he shrugged.

 

"If you were just humming, then I'd love to hear you use your full voice!" she smiled. "Does singing run in your family?"

 

Dean paused before finally answering. "My mom used to sing to me when I was a baby. She used to sing "Hey Jude" by the Beatles to us, and I used to sing with her."

 

"Your mother definitely put you on the right track," Ray said. "I think its beautiful that someone as intimidating and strong as you can have such a gentle but rough tone when you sing. They say that the voice you sing with reflects who you are inside, you know." Dean shrugged.

 

"Dean, how would you feel about being the lead in the school musical?" she asked. Dean almost choked on air.

 

"What? Me? I don't even know what the play is about."

 

"You'd be playing the main character, Evan Hansen. He has social anxiety-"

 

"Social anxiety? What the hell is that?"

 

"Basically, it means you have problems with social things. Talking to people. Relationships. You worry too much of what other people think of you," Ray said. "You can relate, can't you?"

 

"Hell no. I'm proud of myself," Dean said immediately.

 

"Dean, you don't have to lie. I have a Master's degree in psychology," Ray said. "I can see it in your eyes. I saw how you secretly believed what Matt said earlier, even if it was for a second."

 

Dean clenched his jaw. "I-"

 

"Hey Dean?" Sam asked, poking his head around the corner. His cheek was splattered with green on one side and pink on his forehead. "I'm hungry."

 

"What's new?" Dean sighed. "And hey, the project wad to paint on the paper, not on your face."

 

"Sorry, Dean," Sam shot puppy eyes.

 

"Don't give me puppy eyes!" Dean said. "Can I go? I gotta get him home and in a shower and fed. All that."

 

"Only if you take this script home and read it," Ray said, handing Dean a printed and laminated copy of Dear Evan Hansen. Dean looked at it for a moment before taking it.

 

"Fine," Dean said.

 

"You're gonna be in the musical, De? That's awesome!" Sam exclaimed. Dean blushed.

 

"I-I don't know yet! Shut up, Sam!"

 

"Would you like a ride back? The sun is starting to go down. I don't want you two walking back home this late," Miss Ray said.

 

"No, its fine. Thank you though," Dean declined politely. He pulled out his pocket knife. "Got this beauty to protect me."

 

Ray smiled and laughed. "Okay. Here's a 20. Go get him something good." She handed him a fresh 20 dollar bill.

 

Dean eyed her. "You're lucky Sammy needs to eat or else I would curse you out," he said. He looked down and studied the floor. "But uh.. Thanks."

 

"No problem."

 

_________________________________

 

Dean was nervous when the time came a few days later. Auditions were today. He didn't tell any of the guys that he wanted to play Evan. He didn't tell them that he wanted to be in the musical at all.

 

Which he didn't.

 

Duh.

 

"Dean, you're up!" Ray said. Dean swallowed and stood up. He'd never sang in front of anyone before. Ever. There were gasps and looks of shock when he stood up and went on stage.

 

"Um.. I'm auditioning for Evan Hansen," Dean said. There was applause then silence before the music began.

 

_"_

_I've learned to slam on the brake_

 

_Before I even turn the key_

 

_Before I make the mistake_

 

_Before I lead with the worst of me_

 

_Give them no reason to stare_

 

_No slipping up if you slip away_

 

_So I got nothing to share_

 

_No, I got nothing to say"_

 

Dean took a breath and shoved his hands in his pockets. His eyes had closed in fear.

 

_"_

_We start with stars in our eyes_

 

_We start believing that we belong_

 

_But every sun doesn't rise_

 

_And no one tells you where you went wrong_

 

_Step out, step out of the sun_

 

_If you keep getting burned_

 

_Step out, step out of the sun_

 

_Because you've learned, because you've learned_

 

_On the outside always looking in_

 

_Will I ever be more than I've always been?_

 

_'cause I'm tap, tap, tapping on the glass_

 

_Waving through a window_

 

_I try to speak, but nobody can hear_

 

_So I wait around for an answer to appear_

 

_While I'm watch, watch, watching people pass_

 

_Waving through a window_

 

_Oh, can anybody see, is anybody waving?_ _"_

 

His eyes slowly opened. This is the part that he really felt connected with.

 

_"_ _When you're falling in a forest and there's nobody around_

 

_Do you ever really crash, or even make a sound_

 

_When you're falling in a forest and there's nobody around_

 

_Do you ever really crash, or even make a sound_

 

_When you're falling in a forest and there's nobody around_

 

_Do you ever really crash, or even make a sound_

 

_When you're falling in a forest and there's nobody around_

 

_Do you ever really crash, or even make a sound_

 

_Did I even make a sound_

 

_Did I even make a sound_

 

_It's like I never made a sound_

 

_Will I ever make a sound?"_

 

Dean's chest got heavy. He took the breath he knew he needed. The music got more defined.

 

_"_ _On the outside always looking in_

 

_Will I ever be more than I've always been_

 

_'cause I'm tap, tap, tapping on the glass_

 

_Waving through a window_

 

_I try to speak_

 

_But nobody can hear_

 

_So I wait around for an answer to appear_

 

_While I'm watch, watch, watching people pass_

 

_Waving through a window_

 

_Can anybody see, is anybody waving back at me?"_

 

Dean connected eyes with Miss Ray and everyone else when his voice got higher and more dramatic. The music had been flowing through him like it was his blood. He ran his hand through his hair.

 

_"_ _Oooh, is anybody waving_

 

_Waving, waving, whoa-oh, whoa-oh-oh-oh_ _."_

 

There was silence for a moment. Dean's heart raced. What if they didn't like-?

 

The auditorium erupted with applause and cheers. The drama class chanted, "Evan! Hansen! Evan! Hansen!" over and over. Ray leaned into the Mic with a smile.

 

"Welcome to _Dear Evan Hansen,_ Dean. Congratulations."


	2. Chapter 2

**Notes for the Chapter:**

> Dean singing in in Italics
> 
> V singing is in bold and italics

Dean had a smile as he walked out of the drama classroom that lasted him all day. For someone who didn't want to be in the play at all, he seemed pretty damn happy about it.

 

As he turned to leave the school to go get Sam, someone tapped on his shoulder.

 

"Yeah?" Dean asked the girl who stood in from of him. She was a girl who was shorter than him. Her long light brown hair fell over her bright blue eyes and the black thick rimmed glasses that perched on her small nose. She wore faded blue jeans that were tight in all the right places, and her Nirvana hung off of her shoulder just a little.

 

"Hey, I just wanted to say awesome job on getting Evan Hansen. Your voice is so pretty," she said. She looked so shy but so bold at the same time. Dean was definitely intrigued.

 

"Haha, thanks," he smiled. A blush grazed his face. "I'm Dean."

 

"I'm V," she said. "I got the role as Zoe."

 

"That's amazing," Dean answered. "Is V short for Veronica?"

 

"Yeah. I hate that name. It makes me sound like some old cat lady," V rubbed her arm.

 

Dean laughed. "No it doesn't. V is pretty edgy though. I like it."

 

V blushed. "O-oh thank you!"

 

"No problem," Dean said. "I take it you don't get a lot of compliments?"

 

"Nah. It's okay though. I'm the geeky drama kid," V shrugged.

 

"Well that ain't right at all. You're _gorgeous,"_ Dean told her. V looked down and her face was fire red.

 

"Thanks," she smiled.

 

"Hey, I gotta go bring my baby brother to his friend's house. You wanna do some lines with me?" Dean asked.

 

"Sure. Sounds good to me."

 

_________________________________

 

"Who's this?" Sam asked.

 

"Her name's V. She's my costar," Dean answered, smiling.

 

"Costar?" Sam tilted his head. "Wait.." Sam grinned. "You auditioned?"

 

"Yep."

 

"He got the lead, Evan Hansen," V supplied. Sam hugged Dean tight.

 

"That's amazing!" he exclaimed.

 

"Thanks kid," Dean answered.

 

"You gonna be some Broadway kid now?" Sam teased. Dean punched his arm. "Okay I'll stop. Only if you and V sing a song for me."

 

Dean saw the nervousness in V's eyes. "Maybe in a few days. We aren't completely ready yet."

 

"Oh okay," Sam said. "Dean, this is James's house. Bye!"

 

"You got everything?"

 

"Yeah, De."

 

"You'll call me if anything happens?"

 

Sam rolled his eyes. "Yes, Mom."

 

"Damn right I'm your mom. Now, no girls. If he kisses you, no tongue until you're 13 or I'll kick your ass. Got it?"

 

Sam blushed. "Shut up Dean! Bye!"

 

Dean laughed. "Bye."

 

"You seem to be more of a parent than a brother," V said as they walked to the motel.

 

Dean shrugged. "Sometimes I have to be. Its how I've always been."

 

"Always? Sounds like a pretty shitty childhood."

 

Dean laughed. "Yeah. Maybe."

 

He turned back and looked at the house that Sam stepped into. Nervousness fluttered in his stomach.

 

"Hey," V set her hand on his shoulder. "He's gonna be fine. First time letting him go to a friend's house overnight?" He nodded. "He'll be fine, Momma Bear. Just gonna play video games and compare dick sizes."

 

That earned another laugh from him. "The only person that makes me laugh like that is Sammy."

 

"Nice to know I can make you smile," V said. They met eyes for a minute before blushing and turning away.

 

"So you wanna tell me exactly where we're going?" she asked after a few more minutes of walking.

 

"There's this place I found that no one knows that I go to. Its kind of cheesy, but its like my safe place, I guess," Dean answered. "You gotta follow my steps to the tee because if not you'll get hurt."

 

"Okay," she said slowly.

 

"I'm joking. There are a lot of branches though," Dean said.

 

A gate that had vines wrapped around some of the chain came into view. Dean started climbing over it with ease, flipping over the top and landing on his feet. V applauded from the other side, and Dean bowed. V laughed with him and climbed over the gate as well. They kept walking for a little more until they saw a tree with moss hanging off its branches. There were carvings into it that must have been made from a sharp pocket knife. Dean looked so much more relaxed when he sat down on one of the roots. The sunlight caught in his hair enough where V saw the blonde more than ever and the brightness in Dean's eyes stood out. The scene was so perfect. It made V wish she brought her Polaroid.

 

"Wow.. This is.. This is beautiful, Dean," V said.

 

"Yeah, I know. I found this while I was walking around when we got here back in May," Dean replied. "I come out here to calm down and think. Release some anger I don't wanna lash out on some poor bastard."

 

"It's better than the alternative."

 

"No shit. I'm 16 years old and pissed off at the world as it is. Hormones _and_ people pissing off a Winchester? Not a good mix," Dean admitted. "Last school I went to I punched the principal in the face and broke his jaw for asking me if I lived on the street or something. Sammy was so pissed at me. Didn't talk to me for like 3 days. Dad as s a mix of _Damn it, Dean_ and _Holy shit, You knocked the hell out of him_ _. Good job, son._ "

 

"I'd give you a high five, honestly."

 

"Right? Tell Sam that for me, would you?"

 

"I will," V said with a grin. "Ready to rehearse?" Dean nodded.

 

Rehearsing lines with V was so much fun. There was laughing and gasps when they couldn't believe the plot twists and hurtful comments some of the characters made. They went over it for a good 20 minutes before a song titled "If I Could Tell Her" came up.

 

"You ready?" Dean asked. V nodded.

 

"I'm a bit nervous, if I'm honest."

 

"If were about honesty, I am too. Lets just do it as best as we can."

 

" _He thought you were... awesome."_

 

" ** _He thought I was awesome? My brother?"_**

 

_"_ _Definitely!"_

 

**_"_ ** **_How?"_ **

 

_"_ _Well_...

 

_He said_

 

_There's nothing like your smile_

 

_Sort of subtle and perfect and real_

 

_He said_

 

_You never knew how wonderful_

 

_That smile could make someone feel_

 

_And he knew_

 

_Whenever you get bored_

 

_You scribble stars on the cuffs of your jeans_

 

_And he noticed_

 

_That you still fill out the quizzes_

 

_That they put in those teen magazines_

 

_But he kept it all inside his head_

 

_What he saw he left unsaid_

 

_And though he wanted to_

 

_He couldn't talk to you_

 

_He couldn't find the way_

 

_But he would always say_

 

_If I could tell her_

 

_Tell her everything I see_

 

_If I could tell her_

 

_How she's everything to me_

 

_But we're a million worlds apart_

 

_And I don't know how I would even start_

 

_If I could tell her_

 

_If I could tell her_ _"_

 

**_"_ ** **_Did he say anything else?_ ** **_"_ **

 

_"_ _A..about you?_ _"_

 

**_"_ ** **_Never mind, I don't really care anyways.._ ** **_"_ **

 

_"_ _No, no, no..just, no, no..he said..he said so many things, I'm just..I'm trying to remember the best ones. So, um.._

 

_He thought_

 

_You looked really pretty, er.._

 

_It looked pretty cool when you put indigo streaks in your hair_ _"_

 

**_"_ ** **_He did?_ ** **_"_ **

 

_"_ _And he wondered how you learned to dance_

 

_Like all the rest of the world isn't there_

 

_But he kept it all inside his head_

 

_What he saw he left unsaid_

 

_If I could tell her_

 

_Tell her everything I see_

 

_If I could tell her_

 

_How she's everything to me_ _"_

 

The two of them sang together, locking eyes. " _But we're a million worlds apart."_

 

_"_ _And I don't know how I would even start_

 

_If I could tell her_ _."_

 

Dean's voice got more power in it. 

 

_"_ _If I could tell her_

 

_But what do you do when there's this great divide?_ _"_

 

**_"_ ** **_He just seemed so far away_ ** **_"_ **

 

_"_ _And what do you do when the distance is too wide?_ _"_

 

**_"_ ** **_It's like I don't know anything_ ** **_"_ **

 

_"_ _And how do you say_

 

_I love you?_

 

_I love you_

 

_I love you_

 

_I love you_

 

_But we're a million worlds apart_

 

_And I don't know how I would even start_

 

_If I could tell her_

 

_If I could_ _.."_

 

Their eyes stayed connected after the song ended. They moved closer and closer and-

 

_Ringgg! Ringgg!_

 

"Shit!" V exclaimed and grabbed her phone. "Hello? Hey Uncle Jonas... Yeah, I'm sorry. I've been rehearsing lines with Dean.. Dean Winchester.... He's the star of the show... Yeah! I got Zoe..." she blushed. "Shut up! Just because he's Evan, doesn't mean I'm gonna instantly fall desperately in love with him.. Ew! Okay, I'm gonna go. Bye!"

 

"Interesting conversation?" Dean raised his eyebrow.

 

V punched his arm. "Shut up. Anyway, i gotta go. It was nice hanging out with you. Thanks for spending time with a geek like me."

 

"A geek with a beautiful voice and amazing face," Dean flirted lightly. "A geek who I'd like to see again."

 

V blushed again. "I.. Um.. S-sure!"

 

"Cool," Dean answered and stood up. He lead her out of his little world and back over the fence. "I could walk you home if you want."

 

"Nah It's cool. My dad would shoot you," V said. Dean laughed.

 

"I've had enough bullets aimed my way, thanks."

 

"Alright, Batman, calm down," she teased. The two laughed for a minute. Dean pecked her cheek before turning away, starting to walk off.

 

"Later, Zoe," he said over his shoulder.

 

"Have a good night, Evan," she said as she walked. "See you in class tomorrow."

 

"Sounds like a plan."

 


End file.
